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Well I'm thinking you need to define what you mean by succeed. For me success will be earning the same or a little more than what I'm earning currently working for someone else.

That's exactly how I'm defining it. The rest is gravy and empire-building: wonderful perks, but above and beyond the nut.

The type of sacrifices you seem to be talking about are very dramatic. Losing my house, family and everything I own by the sounds of it.

So in other words, there's a limit to what you're willing to put your family through to make your business work. Good. We're making progress!

Now what happens if it takes six months to a year before you're getting consistent work? Or if it takes two years (or possibly much longer) before you come anywhere close to your current salary working freelance? What happens if/when the savings are gone and you're still not breaking even? Got an attorney on board yet? How are you fixed for insurance?

At the end of the day, the question I'm asking is this: if the first six to eighteen months don't work out nearly as you expect, are you prepared (psychologically, emotionally, financially) to carry out a war of attrition? Do you have the ability to stay in the trenches and fight, even when it seems that the war has turned against you? Or are you just blowing that scenario off as unrealistic, focusing only on being "motivated"?

What price are you really willing to pay? Are you even allowing for the possibility that you might have to pay it? At what point do you pull the plug and run back to Da Man?

It's an important question. If you can't answer it, you're not ready to jump.

Now, I understand what you're saying about motivational books or tapes. You can't just read a book to know what you're getting into. But 10 years of experience helping someone else to build and manage their business, a model of the business you are looking to create, has got to be some sort of foundation to start from.

I'd certainly hope so. But then, most of us had foundations to start from - educational, professional, financial - and most of us still had to slug it out. It's the nature of the beast.

The foundation gets you in the door. I've known folks with MBA's and just as much industry experience who rushed into freelance life and got broken hard. Their backgrounds actually served as liabilities: they were convinced that with all those advantages, they couldn't possibly fail. Arrogance kills.

But all she's asked is where to start. She's not opening tomorrow. She's looking for advice. Motivation is a fine thing. But that's not what she's after. She's after real world advice on where to start.

For God's sake, this is where to start! And all I'm seeing here is ducking and weaving, and people trying not to discourage themselves. What part of "do an honest and valid risk assessment" is unclear or offensive as being an extremely important first step to starting a business?

If you were applying for a bank loan to start a business, the bank would be asking very similar questions to these - not quite the way I'm doing it, granted, but they'd want to know what your risks are. If your answer to them was, "Oh, I don't worry about that - I'm motivated, and that's what matters", their next step would be to call security.

So the question remains. What does she need to do next?

Until she does that first step, she doesn't do anything next. Without a clear picture of assets and liabilities - i.e., risk - there's no way on earth anyone here can give practical and useful advice on a case-by-case basis. As someone who has been helping to build a business for ten years, you should know that.

Once a clear picture of risk comes into focus, then the next round of questions make sense. Marketing, asset management, politics, contracts, client management, project management, networking (making and keeping good allies), technology issues - they're all predicated on this one inconvenient little pivot. None of it means a damn otherwise.

Robert – By your initial rant I can only assume that you see the idea of 'freelance' as a bad one.

If I see "freelance" as a bad word, then I have a funny way of showing it. I've been a freelance copywriter full time for six years now, and I work with freelancers every day. Some of my best friends are fellow freelancers. Strange company to keep if I'm down on freelancers, eh?

My point in that first post was that most freelancers pull the plug, quit, fail, give up, usually within two years. Most are pursuing The Dream, and most have advantages - these aren't nitwits we're talking about here. The cold and unpleasant truth is that if you can't afford failure, you can't afford to live this life - you're betting the farm on a hard six.

O.K. what would you suggest. I'm really interested. What should her next step be once she has the belief in the idea of not working for 'the man'.

Is that her (or your) only motivation - not having to work a job? It's not a bad motivation, but it's not enough. Not nearly. Again, there has to be real commitment backing it up.

By the way, if I sound grouchy I don't mean too. Just want to hear something I can use. Instead of rants I've heard a million times.

Ever consider that, just maybe, there's a reason you've heard them so often?

I will just add that the majority of people I've heard these sort of rants from are those that are still struggling. The rest seem more than happy in the paths they took.

By the way, I'm talking about Ninja here. Not me. Other than the 10 years of experience.

My sorry is a good one. I've been working fulltime for 10 years, been freelancing on top of that for about a year and a half. I've got the client base. But it would be nice to drop the fulltime and not have to work both, which equal 16hr days a lot of the time. As you can see I'm no opposed to hard work and I would have made the move earlier. Just waiting for my wife to be able to work again, even part time. (I'd like to have the safety net.) Just having a new baby so I'm happy to wait 6-8 months.

Not plans are perfect, I'll grant you. But that's the larger version of mine. As far as the details are concerned. I've ironed or are ironing them out, contracts, insurance etc.

Personally I have plenty of motivation. That also includes family.
But I always have a back up plan if things don't work just the way I want them to.
No matter what I'm doing. You might not be able to plan for everything, but you can plan for a complete collapse. As long as you are happy where this will put you and those dependant on you. I don't see the problem with going out there and giving it a go.

Personally I have plenty of motivation. That also includes family.
But I always have a back up plan if things don't work just the way I want them to.
No matter what I'm doing. You might not be able to plan for everything, but you can plan for a complete collapse. As long as you are happy where this will put you and those dependant on you. I don't see the problem with going out there and giving it a go.

Then you and I are on the same page. Sorry for any misunderstanding - nothing personal.

Seriously though, for every one of those struggling "woe is me" rants you've read, I must have read a similar "think it and you can do it" wish fulfillment fantasy.. too many folks who dive off the deep end without checking to see if there's water there. Like I said, it gets old. Makes us all look like fly-by-nighters, especially since these same folks will leave their websites up for years after actually quitting, on the hope that somewhere along the line they'll be noticed. These days, the Web is like that strip of near-orbit that's full of space junk, only instead of bolts and spent boosters, it's the websites of failed businesses. The market does not need more dreamers - it needs more committed successes.

These days, someone asks me for advice on getting started, I tell them to go rent and watch the movie "Swimming With Sharks", with Kevin Spacey. It's a movie about a young, wide-eyed and abused assistant to a powerful Hollywood producer, who finally snaps, kidnaps and tortures (yes, tortures) his boss. Great little flick about naivete, bitterness, power and the brutality of the Hollywood machine - and fairly accurate, according to my friends out that way. It's dark and harsh - not a comedy at all - but it gets the point across pretty well. At the end, there's this great little speech, goes something like this:

"Let me tell you something, Jack. Everyone is going to give you the same advice. Tell you that you have to pay your dues, ask you to do them a favor, 'do this for us'. They all want you to play by the rules, Jack. Their rules. But save that candy stripe sh-t for the Wall Street wimps. Because this town is a jungle. This is your inner city, these are your mean streets. And the only interests that you need to protect are yours. And the only needs that you have to serve are yours. So the only question that you need to answer is this - and think about this, Jack.

"What do you really want?"

Overly dramatic for the freelance world? Sure. Solid business advice, however (not to mention an excellent denouement to a great film).

Just as a last thought to this debate, wanted to kick this out there. I was hanging at the local Barnes & Noble tonight, overpriced yet delicious Starbucks in hand, doing some book browsing.. and I discovered that Robert Greene has a new book out! (Actually it came out in January, and I'm deeply embarrassed to admit that I didn't know about it - I'm a Greene fan.)

Had to buy it. Like I said, big Greene fan - have been, ever since "48 Laws of Power". His followup ("The Art of Seduction") was pretty good, but "48 Laws" has served me admirably many times in this business. It also saved my butt more than a few times. ("48" was mainly about politics; "Seduction" was mainly about sex and influence. "War" takes the same approach with strategy and tactics, both on the battlefield and in the boardroom.)

Reading through "War" tonight, this is exactly the kind of book that should be on the shelf of anyone considering a dive into self-employment. Practical, unsentimental, direct, every thesis backed up with historical precedent. Highly recommended to all.